| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 5/17/25 | Shkendija vs Sileks | First League | 1:3 | Yes | Yes |
| 2/23/25 | Shkendija vs Sileks | First League | 4:2 | Yes | Yes |
| 10/5/24 | Sileks vs Shkendija | First League | 0:0 | No | No |
| 4/14/24 | Shkendija vs Sileks | First League | 6:1 | Yes | Yes |
| 12/10/23 | Shkendija vs Sileks | First League | 3:1 | Yes | Yes |
| 9/17/23 | Sileks vs Shkendija | First League | 2:1 | Yes | Yes |
| 4/26/23 | Shkendija vs Sileks | First League | 0:0 | No | No |
| 10/30/22 | Sileks vs Shkendija | First League | 1:1 | No | Yes |
| 8/14/22 | Shkendija vs Sileks | First League | 1:1 | No | Yes |
| 4/4/21 | Shkendija vs Sileks | First League | 2:1 | Yes | Yes |
| 2/21/21 | Sileks vs Shkendija | First League | 1:2 | Yes | Yes |
| 11/25/20 | Sileks vs Shkendija | Macedonian Cup | 1:0 | No | No |
| 10/3/20 | Shkendija vs Sileks | First League | 1:1 | No | Yes |
| 2/23/20 | Sileks vs Shkendija | First League | 0:0 | No | No |
| 10/23/19 | Shkendija vs Sileks | First League | 3:0 | Yes | No |
| 8/18/19 | Sileks vs Shkendija | First League | 1:0 | No | No |
| 5/8/19 | Shkendija vs Sileks | First League | 0:0 | No | No |
| 3/28/19 | Sileks vs Shkendija | First League | 0:3 | Yes | No |
| 11/22/18 | Shkendija vs Sileks | First League | 5:0 | Yes | No |
| 9/23/18 | Sileks vs Shkendija | First League | 1:2 | Yes | Yes |
| 6/6/18 | Sileks vs Shkendija | Friendly International | 3:0 | Yes | No |
| 5/28/18 | Shkendija vs Sileks | Friendly International | 2:2 | Yes | Yes |
| 3/26/18 | Shkendija vs Sileks | Friendly International | 5:0 | Yes | No |
| 11/16/17 | Sileks vs Shkendija | First League | 0:2 | No | No |
| 9/20/17 | Shkendija vs Sileks | First League | 5:0 | Yes | No |
| 4/23/17 | Sileks vs Shkendija | First League | 1:1 | No | Yes |
| 2/19/17 | Shkendija vs Sileks | First League | 2:0 | No | No |
| 10/16/16 | Sileks vs Shkendija | First League | 1:3 | Yes | Yes |
| 8/8/16 | Shkendija vs Sileks | First League | 2:1 | Yes | Yes |
| 5/8/16 | Shkendija vs Sileks | First League | 3:0 | Yes | No |
| 4/6/16 | Shkendija vs Sileks | First League | 3:1 | Yes | Yes |
| 12/6/15 | Sileks vs Shkendija | First League | 3:1 | Yes | Yes |
| 9/27/15 | Shkendija vs Sileks | First League | 3:1 | Yes | Yes |
| 5/6/15 | Sileks vs Shkendija | First League | 0:2 | No | No |
| 4/4/15 | Sileks vs Shkendija | First League | 0:3 | Yes | No |
| 11/23/14 | Sileks vs Shkendija | First League | 0:1 | No | No |
| 9/14/14 | Shkendija vs Sileks | First League | 3:0 | Yes | No |
| 4/3/13 | Shkendija vs Sileks | First League | 3:0 | Yes | No |
| 3/31/13 | Sileks vs Shkendija | First League | 2:3 | Yes | Yes |
| 10/28/12 | Shkendija vs Sileks | First League | 1:0 | No | No |
| 4/29/12 | Sileks vs Shkendija | First League | 1:4 | Yes | Yes |
| 12/11/11 | Shkendija vs Sileks | First League | 2:1 | Yes | Yes |
| 9/17/11 | Sileks vs Shkendija | First League | 1:4 | Yes | Yes |
| 4/10/11 | Shkendija vs Sileks | First League | 1:0 | No | No |
| 11/27/10 | Sileks vs Shkendija | First League | 1:1 | No | Yes |
| 8/29/10 | Shkendija vs Sileks | First League | 3:0 | Yes | No |
| 4/23/08 | Shkendija vs Sileks | First League | 1:2 | Yes | Yes |
| 11/25/07 | Sileks vs Shkendija | First League | 1:1 | No | Yes |
| 8/26/07 | Shkendija vs Sileks | First League | 0:1 | No | No |
| 4/29/07 | Sileks vs Shkendija | First League | 6:0 | Yes | No |
| 3/4/07 | Sileks vs Shkendija | First League | 0:0 | No | No |
| 10/15/06 | Shkendija vs Sileks | First League | 2:1 | Yes | Yes |
| 5/14/06 | Shkendija vs Sileks | First League | 2:2 | Yes | Yes |
| 12/11/05 | Shkendija vs Sileks | First League | 4:1 | Yes | Yes |
| 9/25/05 | Sileks vs Shkendija | First League | 1:1 | No | Yes |